The present invention is directed to certain novel nitroamine compounds and to their utilization in the formation of novoldiamine, compound required to form the antimalarial drug, chloroquine.
Novoldiamine is presently prepared by a complex synthesis. The compound is prepared commercially from 2-diethylaminoethanol and ethyl acetoacetate. The alcohol is reacted with thionyl chloride to form 2-chlorotriethylamine (A) while the acetoacetate is reacted with sodium ethoxide to provide the sodium derivative of ethyl acetoacetate (B). The initially formed compounds A and B are then condensed to yield an intermediate ester which must be hydrolyzed and then decarboxylated to provide 5-diethylamino-2-pentanone (C). This product (C) is hydrogenated in the presence of ammonia to produce the subject novoldiamine product. Other modes of preparation are known (See U.S. Pat. No. 2,365,825), but are not practiced due to the complexity of the synthesis.
It is an object of the present invention to provide certain novel nitroamine compounds.
It is a further object of the present invention to provide a simple and economical method of producing novoldiamine by utilizing certain novel compounds fully described hereinbelow.